Remember the dead or alive game Howard Stern used to do? I think it was Stern. Not sure if he’s still doing it because I’m too cheap to subscribe to Sirius for the total of 5 minutes I spend in the car driving between coffee shops. Pen testing has been under fire lately. Ranum has been talking for years about how pen testing sucks. Brian Chess also called pen testing dead at the end of 2008.

It’s almost two years later and the death of pen testing has been greatly exaggerated. Pen testing is not dead. Not by a long shot. But it is changing. And we have plenty of folks weighing in on how this evolution is taking place.

First off is the mouth from the South, Dave Maynor. OK, one of the mouths from the South, because I suspect I am another. Dave made some waves regarding whether to use 0-day exploits in a pen test, and then had to respond when everyone started calling him names. Here’s the thing. Dave is right. The bad guys don’t take an oath when they graduate from bad guy school that they won’t use 0-days. They can and do, and you need to know how you’ll respond. Whether it’s part of a pen test or incident response exercise doesn’t matter to me. But if you think you don’t need to understand how you’ll respond under fire, you are wrong.

Second, I got to attend a great session by Dave Kennedy and Eric Smith at BSides Atlanta about strategic pen testing. It was presented from the viewpoint of the pen tester, but you can apply a lot of those lessons to how a practitioner runs a pen test in their organization. First off, a pen test is about learning where you can be exploited. If you think it’s about checking a box (for an audit) or making yourself and your team look good, you’ve missed the point. These guys will break your stuff. The question is what can you learn and how will that change your defensive strategies?

The pen testers need to operate in a reasonable semblance of a real wold scenario. Obviously you don’t want them taking down your production network. But you can’t put them in a box either. The point is to learn and unless their charter is broad enough to make a difference, again you are wasting your time.

Finally, I’ll point to a presentation by Josh Abraham, talking about his “Goal Oriented Pentesting” (PDF) approach. It’s good stuff. Stuff you should know, but probably don’t do.

What do all these things have in common? They talk about the need for pen testing to evolve. But by no means are they talking about its death. Listen – at the end of the day, whether you are surprised by what an attacker does to your network is your business.

I still believe pen testing can provide insights you can’t get any other way. I think those insights are critical to understanding your security posture. Those enlightened organizations whihc don’t pen test do so at their own risk. And the rest of us should thank them – they are the slow gazelles and the lions are hungry.